


Anytime

by RittaPokie



Category: Critical Role (Web Series)
Genre: Blowjobs, Edging, Other, Tail Kink, handjobs
Language: English
Status: Completed
Published: 2020-10-19
Updated: 2020-10-19
Packaged: 2021-03-08 22:08:17
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,642
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27103966
Author URL: https://archiveofourown.org/users/RittaPokie/pseuds/RittaPokie
Summary: Molly was having some fun alone, but his tail got twisted up, and Caleb has to help him out.
Relationships: Mollymauk Tealeaf/Caleb Widogast
Comments: 4
Kudos: 104





	Anytime

"Mollymauk." Caleb says, looking up to where the tiefling seems to be trying to literally sink into the pillow.

"Hm?" Molly shifts just so one eye is visible. "Yes, Mr. Caleb?"

"Could you... try and be still?" he asks, gesturing to Molly's tail, which is flicking and twitching despite the knot.

"I need you to know that I am." Molly says.

Caleb takes a deep breath and lets it out. "Okay." he says, and then again, "Okay."

He puts a hand firmly on Molly's tail just below the tie and tries to hold it still, though it feels a bit like a wriggling snake. He tries to focus on that interpretation of it. He *tries*. He loops a finger under the fold that goes into the loop and tugs it up gently. It goes pretty smoothly until the spade gets caught in the knot and then there's resistance and it _tugs_ and Molly makes a _noise_. Molly keens, mostly muffled into the pillow, and the bed bounces as his hips jerk involuntarily.

"Sorry- sorry..." Molly says, lifting his face up, gasping a bit. "Sorry."

"It is fine." Caleb says quickly, and clears his throat. With one last little pull the spade comes free and the problem is resolved. Caleb feels... disappointed.

"Well, uh, I guess that's that." Molly says.

"Ja." Caleb says. When he looks back to Molly, dragging his gaze from that _infernal_ (literally) tail, the tiefling's face is a deeper shade of pink-violet than Caleb has ever seen, and Molly's eyes are hazy, half-closed. "Ja, that is... it is..."

Caleb's fingers twitch in his lap, his eyes trained on Molly's. Molly bites his lip and breaks the contact first, the violet blush spreading up to his ears, down his neck and chest where he's half-turned to face Caleb. 

"Thank you, Mr. Caleb."

"You are welcome, Molly." Caleb says. "Any time."

"Any time?" Molly asks, a smile spreading on his face as he returns his gaze to Caleb's. "Careful now, I might take you up on that."

“Oh?” Caleb asks. His knuckles brush lightly against the outside of Molly’s thigh, and his expression is thoughtful. “Molly… may I-“

“Yes. I’m not entirely sure what you’re about to say- I’ve got a pretty good idea, but yes. Whatever it is, yes.” Molly says before he can finish. “Especially if the end of that sentence is ‘touch you’.”

Caleb situates himself more comfortably on the bed, no longer ready to leave at any second. He can feel his heart hammering in his chest as he settles between Molly’s splayed thighs. The tiefling’s tail flicks and twitches next to him, but he ignores that for now.

He can’t say he has never thought about this. Molly is.. attractive, to say the least. Caleb leans up over him, avoiding eye contact with the tiefling, who he can tell is watching him intently, looking over his shoulder. Caleb presses a kiss between Molly’s shoulders, and trails them down spine, stopping just above the base of his tail. Molly squirms a bit, and moans when Caleb grabs the base of his tail.

“You had quite a reaction, before…” Caleb says, “when the spade was pulled.”

“Yeah, it felt nice,” Molly says in a rush of air. “Please…” he shifts on the bed again. He hadn’t exactly been far away from his climax when the _incident_ had occurred.

“Ah, turn over?” Caleb asks. Molly complies immediately, and Caleb releases his hold on the tail so that he can. Molly arches his back now that he’s on display, his cock twitching against his stomach.

Caleb’s mind races with possibilities, and he doesn’t know where to start. He supposes the basics are as good a place as any. He wraps his fingers around Molly’s cock at the base, and strokes him firmly. Molly sighs in relief, finally getting _something_.

Molly pants, his breathing speeding up, canting his hips into Caleb’s touch, and reaches up to pinch his own nipple, twisting between a thumb and forefinger. He has to stop and grip the headboard when Caleb takes hold of his tail again, this time just below the spaded tip.

Caleb presses his thumb into the dip along the edge of it, tracing the outline with a firm touch, and Molly makes a punched out noise as he comes suddenly, spilling over Caleb’s fingers.

“Who knew?” Caleb says quietly to himself, though Molly can hardly hear him over the ringing in his ears.

“That was…” Molly starts, the words coming out in a mumble. He blinks, clearing his eyes to see Caleb sitting back on his heels, his hands laid idle in his lap.

“Thank you, Mollymauk,” Caleb says.

“I- thank you too,” Molly says. He props up onto his elbows as Caleb makes to slide off the bed. “Hey, wait. Where are you going?”

“Oh, I-“ Caleb looks genuinely confused. “You are finished, are you not?”

“Are you?” Molly asks.

“You… do not have to feel obligated to me, Mollymauk,” Caleb says.

“Come here,” Molly says, and he holds out his hands to Caleb, sitting up. Caleb sits back down on the edge of the bed. Molly’s hands fall lax beside him, and he frowns. Instead, he shifts until he is behind the wizard, his legs hanging off the bed on either side of Caleb’s.

“Now,” Molly purrs in Caleb’s ear. “What would you like?”

“I-ehm…” Caleb mumbles, his face suddenly hot. He finds it very hard to concentrate on answering as Molly plants wet kisses to his neck, and sucks just below his ear. His eyes flutter closed, and he tilts his head to give the tiefling better access.

Without instruction, Molly undoes the buckle of Caleb’s belt and loosens the laces so that he can slide his hands under the hem of his pants. Caleb hisses and arches his hips up slightly. Molly ignores his hardened length for the moment, focusing on his balls instead, squeezing lightly and rolling them in his hands.

Caleb stifles a groan by biting his lip. “Molly-“ he whines, his hips jerking uselessly against the air. Molly draws his hands back up, under Caleb’s shirt, to toy with his nipples. Caleb’s head falls back against his shoulder, and he can see the redhead’s Adam’s apple bobbing as he swallows.

“Do you like being teased?” Molly asks.

“Ja,” Caleb says, his voice more hoarse than usual.

Molly trails his tongue over the shell of Caleb’s ear and twists a nipple in his fingers. He can see Caleb’s cock twitching, still half in his trousers, and Caleb squirms.

Molly takes him in hand, stroking him with a loose grip from base to tip, his thumb swiping at the precum that had formed there. Caleb moans softly, too caught off guard to try and silence himself, and pants as Molly jerks him off quickly. Caleb is surprised that he is allowing himself to get lost in this, allowing himself this pleasure. At the same time, can he really be blamed?

Molly works him until his breaths are coming in short gasps, his hips twitching into Molly’s hand. His vision starts to go foggy, and then, suddenly, Molly lets go. Caleb practically mewls, squirming against the nothing he’s left with. Molly kisses at his neck and cheek softly, petting his hair to calm him back down.

“Molly… please…” he gasps out.

He finally meets Molly’s eyes to see wild mischief there, and Molly slips from behind him and off onto his knees, in front of Caleb. Caleb swallows thickly, his cock jumping at the sight. 

“Oh,” Caleb stutters out, staring down at Molly knelt between his thighs. Molly takes Caleb’s length into his mouth, his fingers wrapped loosely around the base to hold him steady, and bobs his head quickly. Caleb’s vision crosses and he lets out a shaky groan.

“ _Molly_ ,” Caleb says in warning, because he won’t last like this. “Schatz, I can’t…” he pants, and his arms shake as he slides a bit further back onto the bed. He has to focus entirely on holding himself still, so he doesn’t jerk his hips and gag the tiefling. Gods know that he doesn’t want him to stop if he doesn’t want to.

Molly ignores his warning and only sucks harder, his tongue moving over the sensitive underside. If he wanted to pull Caleb apart at the seams, he’s getting what he wanted.

Caleb’s thighs shake, and his brow furrows as he tries to _hold on_. The sharp, white hot spike of pleasure in his gut is chasing everything else from his mind, and he isn’t ready to lose that yet. “Molly, Molly-“ he pants, his knuckles white as he clenches his fists in the sheets behind him.

The gods themselves couldn’t stop him from falling over the edge. His body curls forward, his thighs shaking as his finishes. Molly swallows around him, making him whine pitifully.

Molly pulls back happily, feeling quite powerful. Caleb falls back onto the bed, his mind blissfully empty for the moment. Molly climbs back up onto the bed and straddles Caleb’s lap, watching him come down. He looks years younger without his face drawn in the ever-present, low burn of anguish.

Caleb’s eyes blink open and he stretches, humming at the leftover ache in his core. “You…” he says, and a blush paints his cheeks as a wave of shyness takes him. “You were amazing…”

“Well, thank you,” Molly beams. “So were you.”

The praise lights Caleb’s heart, but he can feel the tendrils of darkness slipping back over his head. He pushes them back for now. Selfishly, he wants this moment for himself. He wants to see Mollymauk sitting over him with a smug smile, feel the low burn of his orgasm in his belly, and just enjoy this. He can and will feel guilty about it later, but not now.


End file.
